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You are here: Home / Virginity sex stories / Jennifer Tests Her Wings by Reefkeeper

Jennifer Tests Her Wings by Reefkeeper

ReefkeeperReefkeeper July 14, 2024 Leave a Comment

“Sure enough Mr. Leaback.”

When they got to the street the valet was already waiting at the curb next to a red Ferrari. The car was turning quite a few heads. She mentioned it to Jimmy.

“Bullshit! It’s you that’s turning all the heads. The car’s simply a nice accessory.”

Jenn did a mock curtsey just before she got in.

—-

He pulled up in front of the hotel. Jimmy said, “I understand you have obligations but I kind of wish we were pulling up to a club where we could go dancing instead.”

Jenn reached over and kissed him a quick peck on his cheek. “I appreciate your understanding and all, but I wish this was the front of your apartment building.” He followed her peck with a more aggressive one. She wished she could spend her night with him instead of fucking Charlie, whoever Charlie is! Oh well!

Jennifer walked straight through the lobby as if she were heading for the hotel restaurant but after she was out of the line of sight of the front desk she turned a corner and headed to the bank of elevators. She thought it made sense to learn how to keep as low a profile as possible if she intended to fuck every guest in the hotel. She boarded the elevator on her way to room 716.

Jennifer knew that she’d encounter some difficult situations if she pursued this line of work (or ‘hobby’ as she liked to think of it), but most of the problems she’d anticipated involved dealing withdifficult johns. She was prepared for johns who were rude, abusive, or had poor personal hygiene, but she was completely unprepared for Charlie.

Charlie was polite, courteous, and considerate, in short he treated her like a lady from the moment she entered his room. He had already put her money in one of the hotel envelopes so she wouldn’t be reminded of her status in their relationship. The way he spoke, the colloquiums he used, his mannerisms, even the way he tossed his head to flip errant hair out of his eyes, everything about him seemed to instantly set her at ease, but the idea of having him touch her seemed repulsive to her.

It made no sense to her. Shereally liked Charlie but was having a huge degree of difficulty getting into the frame of mind to become intimate with him. Then, as Charlie was getting them some wine to drink, he tossed a comment over his shoulder aimed at her and she figured it out. She started laughing and Charlie gave her a puzzled look. “What’s so funny?”

“Oh Charlie, I just realized something and it struck me as being hilarious. Ever since I set foot in your room I felt totally comfortable. I don’t know that anyone has ever made me feelso at home so quickly, but for some strange reason I was having trouble getting into the mood for our evening’s fun and games.

Then it just struck me. You’re my father! Your general appearance, mannerisms, mode of speech, sense of humor, they’re all identical. That explains my being totally at ease with you, but it also explains why I felt funny about the concept of getting naked in front of you.”

“I guess that means that either I’ve got to start acting differently or you have to start getting into the concept of incest.”

Jennifer walked over to Charlie and put her arms around him. “Don’t you dare act differently”! She kissed him with quite a bit of tongue. “Not that I know what the problem was I’m sure I’ll be fine. Either that or as you say…” She placed his hand on her breast. “I’ll just have to get used to fucking dear old Dad!”

Jennifer pushed Charlie onto his back on the bed and began to strip. She’d seen enough movies with strippers in them that her moves were pretty good. Charlie certainly seemed to approve as she shed her red dress revealing her new $400 lingerie. His eyes were glued to her every movement. Jenn unhooked her bra and leaned over him letting her nipples graze his lips. As he began to take each one, in turn, between his teeth his hands went to her panties. While his left hand explored her clit beneath its hood his right hand worked the panties down her legs.

While Charlie worked on her, Jenn undressed him. After she pulled his pants to the floor she dropped to her knees and started licking the head of his cock. It didn’t take Charlie long before he had rolled Jenn over onto her back and started fucking her.

Then it was over. He kissed her before rolling over. “That was great, honey. I can’t wait for my wake-up encore.”

Jennifer’s legs were still spread and her breathing had not yet returned to normal when she heard the measured sounds from the pillow next to her. He was asleep. Jenn looked at her watch and realized that it wasn’t even an hour since she had walked in the door to this room. She quietly slipped out of the bed and headed for the bathroom to finish getting herself off. She smiled as she thought, ‘Mom smiles all too often in the morning for Dad to be this quick. At least that’s one major difference between Charlie and him!’

Between Jenn’s trip to the bathroom and six thirty the following morning Charlie seemed to discover the closet in which he had hidden all the energy he hadn’t had the previous evening. Charlie started caressing her and Jenn awoke to the delightful sensation of his head buried between her legs. By the time she was aware of what was going on she was half way toward her first orgasm of the day.

When she came Jennifer could feel herself squirting into Charlie’s mouth yet he only increased the pace of his mauling her clit with his tongue. Without removing his tongue he slipped two fingers into her. She thrashed from side to side, her hands rapidly shifting from grabbing Charlie’s hair, then her own nipples, her mouth, her own hair, all as wave after wave crashed over her. Jennifer grabbed a pillow and screamed into it as her heels dug into Charlie’s shoulder blades, giving her the leverage to drive her cunt into his mouth.

Charlie flipped her over and as he kneeled between her legs he grabbed her hips and entered her doggie style. Jenn continued to scream into the pillow as his balls slapped into her exposed clit.

After two more in what seemed to Jenn like an endless string of orgasms, Charlie removed his cock and started rubbing its head against her anus. Jenn froze. This was one act she had always thought to be on heroff limits list but Charlie had her in such a state of arousal that all she finally thought to herself was ‘okay, another first!’ It felt like Charlie had grown to baseball bat proportions as his cock entered her virgin ass. After entering her he paused to let her get accustomed to his size. It was Jennifer who finally began the first movement as she began to slam her butt back against Charlie.

—-

Jennifer awoke spooning in Charlie’s arms. She liked it there. She thought back to the previous evening and smiled to herself when she remembered her disappointment in his earlier performance. She realized she was wearing the same grin she’d frequently seen on her mother’s face all those mornings. Maybe there were more similarities between Charlie and her dad than she had thought!

He spoke to her. “At last you’re awake.”

“I’m awake.”

“I’ve been watching you for over an hour. You’re quite lovely as you sleep.”

“What time is it?”

“Around eleven, are you in a hurry to get somewhere?”

“Not at all. It’s just that I thought you had a ten o’clock appointment.”

“I did. I took the chance of waking you up and called in, I think ‘indisposed’ was the word I used.” He chuckled. “It was particularly noteworthy as I was the featured speaker!”

“Will you get in any trouble over it?”

“Doubtful, since I own the company. My assistant is working on rescheduling my talk for one of the other meetings. Ben Roberts is the head of one of my branch offices.”

Jennifer rolled over in his arms and kissed his chin. “Oh! So I’m entertaining the big boss!”

“And doing an excellent job I might add.

Want to go out and get some brunch?”

“I’d love to but all I have to wear is the dress I had on last night.”

“Ben said you were just moving around until your friend comes home on Tuesday. Where are your things?”

Jennifer adopted an embarrassed look. “Checked at Penn Station.”

“Not to make this sound too much likePretty Woman, but why don’t I hire you until Tuesday morning? Then you can keep your things here.”

“How much would you pay me?”

“Oh, let’s see, 48 hours or so, at $75 an hour would be $3,600 but since I’d want you to be exclusive to me, oh let’s say $100 an hour. How about 4,800 dollars?”

“Done! Also not to sound too much like the movie but I would have done it for half that.” She kissed his nose.

“So it’s my turn to say that I enjoyed last night so much that I would have paid double!” He squeezed her ass as he shook his face between her breasts. “But you’d better get up so we can feed ourselves. There’s a shop in the hotel where you can pick up an outfit for brunch. After we’ve eaten you can go to Penn Station to retrieve your things while I hit a meeting.”

Jenn jumped out of bed. “Sounds like a plan!”

—-

Charlie took her to a place on the west side that served a champagne brunch and overlooked the river. Jennifer wanted a Mimosa with her brunch so she dug out a fake I.D. Carrie had given her for her eighteenth birthday but the waiter never asked to see it. She was mildly disappointed.

“So have you decided yet where you want to go to college?”

“It’s not set in stone yet but I’ve been accepted into Cornell’s Veterinary School and I’ve had my heart set on getting my DVM since I was about eight!

And you have a Real Estate Company!”

“Yes, we’re about the biggest independent in the state of Alabama. Speaking of that, since you’re my newest employee and I can’t spend all day doing what I’d most like to do with you, here’s my secretary’s card. While I’m in the meeting this afternoon I want you to liaise with her and work out the best time for me to give my little talk. I definitely want it to happen before I leave for home.”

Jenn put the card in her purse. “This is a nice restaurant. Have you ever been fucked in its men’s room before?”

Charlie smiled. “No and I’m not going to be now. Missing one meeting is spontaneous and fun loving but missing two is irresponsible.

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